Classic Chianti: Florence to Siena

On this tour not only will you have the chance to explore the two great medieval cities of Florence and Siena, but you will also take hikes following trails through classic and timeless Chianti landscapes. It's perfect for anyone who hikes regularly and wants to explore at their own pace. There are plenty of places of historic interest to discover amidst picture-postcard scenery, and many chances to visit vineyards along the way, all coupled with comfortable and welcoming accommodation, and mouth-watering food and wine. There are ups and downs to the hill towns, due to the nature of the rolling Tuscan scenery. It’s best to train ahead of time to do some with practice hikes that include stairs and ascents and descents like those you will experience on the trip while carrying your day bag. There are a couple optional loop hikes that can be sat skipped if a rest day is needed. If time allows, then we’d suggest adding an additional day at the end of the trip in historic Siena to soak up the atmosphere and rejuvenate before continuing with onward travel.

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.

Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&Bs, inns, and guesthouses.

Solo Travellers, Families with Teens

The minimum age for this tour is: 12 Years

This trip is graded ‘easy to moderate’ overall. The terrain is hilly with regular ascents and descents, and summer temperatures can be high. You should therefore be in good physical fitness to fully enjoy the hiking on this trip. Most of the route follows gravel and farm tracks and trails, and minor roads from time to time. It’s best to train ahead of time and do some practice hikes including stairs and ascents and descents like those you will experience on the trip while carrying your day bag. The walks are an average of 15-16km (9.3-10mi) each day and a couple of them are optional and could be skipped if an additional rest day is required. However, should you also wish to skip a hike between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.

Stay in charming small hotels, guesthouses and agriturismos. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute. All are located in glorious settings, be it a town, a hamlet, or the wonderful city of Siena

Additional Nights

Many of our hikers choose to add extra nights along the hike to sample more of the wonderful hiking and attractions available in Chianti. If time allows, then we would recommend adding an additional night at the end of the tour in Siena to further explore this iconic city.

Solo Hikers & Single Rooms

This trip is available to solo hikers, although there is a supplement due to the fact that some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.

Meals

The delicious Chianti food and wine are undoubtedly a highlight of this vacation.

Breakfast is included each morning and normally consists of a traditional European style continental breakfast or buffet breakfast that often includes coffee, tea, yogurt, granola, meat, cheese, and baked goods. In some cases, a hot dish (eggs, pancakes, etc.) will be served or offered.

Lunches and dinners are not included in this trip. We recommend finding cafés or restaurants located in the towns or along the walking route, or to purchase snacks and a picnic lunch to bring along on the hikes from local supermarkets and markets. Alternatively, most accommodations will be happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or nearby restaurants. Further details can be found within your Information Pack and the Macs Adventure Smartphone App.

The route is not waymarked, except for some sections on dedicated trails. However, we provide the Macs Adventure Smartphone App making it simple to follow the route using a smartphone. Rest assured that by downloading the route maps in our app, that this will continue to work even in areas without any mobile or internet reception.

This trip is available to start anytime between April and October.

Peak Season Availability

As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates. Availability in Siena is very challenging around the times of the 'Palio' horse races, which are held annually in early July and then again in mid-August over the course of 4 days each month.

Time of Year

The Spring months offer warm sunshine, fewer crowds, and pleasant hiking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favorable time of year, boasting cooler weather and a striking landscape made up of fall colors. July and August are good months to go but can be very hot for hiking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. The towns and villages are very vibrant at any time of year, which makes for a great atmosphere, yet as soon as you get on the hikes its relatively quiet and peaceful.

This trip starts in Florence. To reach Florence, we recommend flying into Pisa Airport (PSA) or Rome Airports (FCO or CIA). There is also an airport in Florence (FLR), however, flights in and out of this airport are limited.

If arriving in Florence, you can reach the city center by train or bus within 15-20 minutes.

If arriving in Pisa: From the airport take the PisaMover that departs approx. every 10min to the Pisa Centrale Train Station (takes 5 minutes). After exiting Arrivals, follow the signs for the PisaMover, turning left and walking along the passageway to the little Pisamover station at the end of this passageway. You can either take the stairs up or go up to the platform with the elevator. Once upstairs you can buy a ticket from the machine. From Pisa Centrale Train Station, trains to Florence leave around every 30min, and the journey takes approx. 1H15.

If arriving in Rome (note Rome has two airports): From Rome Fiumicino Airport (FCO), take the Leonardo Express Train that’s located inside the airport and departs every 15min to the central train station Roma Termini (takes about 32min). From Ciampino Airport (CIA), there’s a bus to Roma Termini (takes about 40min). From Rome’s Roma Termini Train Station, trains to Florence leaves several times a day, and the journey takes approx. 1H36.

Please check the Trenitalia website for timetable planning. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.

If you’d prefer to avoid public transport from the airport, a private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply). Once your trip is confirmed please share your flight information with us, including your arrival time, as soon as you have booked your flights, so that we have those details well in advance and we can arrange the transfer for you ahead of time. 

It's easy to travel from Siena by train to the major airports of Florence, Pisa, and Rome.

The Siena Train Station and Bus Station are located in the valley below the city center. (about a 2km/1.25mi walk from the majority of accommodations we use). To make your way to the station you have a few options (each payable locally): 1) take the escalators 2) take a bus or 3) take a taxi.

Approx. total journey times from Siena are:

To Florence 2H15 – 3H15

• The train to Florence Santa Maria Novella station is usually a direct train that goes via Empoli and takes around 1H30. Some trains are direct whereas others go via Empoli.

To Rome 2H15 – 3H20

• To Roma Termini Train Station it’s normally necessary to change trains in Florence or Chiusi-Chianciano Terme and takes around 3H30.

To Pisa 2H00 – 3H15

• To Pisa’s Train Station there is usually a train that departs approx. every 30min that goes via Empoli and takes around 1H45.

Once again it will be necessary to travel from the central train stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this).

Alternatively, we can arrange a taxi from Siena to your departure city or airport. Please let us know in advance if you wish to include this option for an additional fee.

Please check the Trenitalia website for timetable planning. There are also local buses that you can take for your onward travel and you can find the information here. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.

One bag of up to 20kg/44lbs per person will be transferred from each accommodation to the next.

At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase.Your booking includes transfer of 1 bag per person.  It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.